


Girl Like Me

by eri_quin



Category: Pocket Monsters | Pokemon (Anime), Pocket Monsters | Pokemon - All Media Types
Genre: Age Difference, Alternate Universe - Always a Different Sex, Alternate Universe - Gender Changes, Cunnilingus, Deepthroating, F/M, Face-Fucking, Face-Sitting, Genderbending, Kinktober, Kinktober 2019, Older Man/Younger Woman, tongue-fucking
Language: English
Status: In-Progress
Published: 2019-10-03
Updated: 2020-06-03
Packaged: 2020-11-22 09:49:29
Rating: Explicit
Warnings: No Archive Warnings Apply, Underage
Chapters: 11
Words: 14,970
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20872220
Author URL: https://archiveofourown.org/users/eri_quin/pseuds/eri_quin
Summary: Giovanni was stuck in that masquerade ball, bored and annoyed. He meets a mischievous young woman, and suddenly the Meteonite and Team Plasma didn't mean a thing."Cinderella had to go, huh?"He wanted to play cat and mouse and chase after her, and he was determined to find out who she was.Kinktober 2019; fem!Ash; ShatterShipping“Ah, time’s up,” she said in disappointment. “Cinderella’s got to go, you know?” she said playfully, her fingers slipping at the edges of her mask.She threw it at his face, causing him to reach and catch it, busied by trying to keep it from hitting his eyes and blinded at that moment.When he looked back to her, she was already gone.





	1. Day One: What's Up, Danger

**Notes for the Chapter:**

> 1\. Deep-Throating | Inflation | Face-Sitting | Masks  
Prompts Chosen: Deep-Throating, Face-Sitting, Masks
> 
> Playlist:  
Bad Guy by Billie Eilish  
A Moment’s Silence by Hozier

“_A masquerade?_”

If Giovanni sneered any harder, he was sure that his face would get stuck this way. But honestly! What kind of operation was he running?

“Think of it this way,” Ariana rolled her eyes. “Gives our operatives a break and reward for their hard work. Hard work that has been _good_ work. And it’ll be fun,” she added with a smirk.

Giovanni huffed and resisted the urge to massage his head. “Very well. Just…organize it yourself. I’m going to have a drink or something.”

He strolled away from her and thought that would be that.

Except it wasn’t, not when he found himself attending the fucking masquerade ball and wearing one of those stupid masks. If his Team wanted to infiltrate it, they could’ve done so themselves! They didn’t have to drag him into it. All he’d wanted was the Meteonite.

“Ridiculous,” he scoffed, nursing a glass of wine and wishing for something stronger.

Maybe he could just…leave. It wasn’t like he was recognizable, mask and all. Plus, he was alone and everyone was too busy to notice or care. All of the elite of Unova were there though and maybe a little reconnaissance wouldn’t be too bad…

“Alone tonight?” a voice said lightly and he turned to face the intruder to his thoughts, perking up at what he saw.

Shorter than him, the young woman who wore the long black dress, fitted to her body, captured his interest immediately. Especially wearing the deep red masquerade mask on her face, honey colored eyes not at all hidden by it.

But the mischievous smile on her face drew him in.

“I might be,” he said idly, swishing the wine in his glass slowly. “Are _you_?”

She laughed lightly, ending up grinning freely at him. “I am. I’m hoping you are, if I can be so forward as to say.”

She certainly was forward! But she was interesting and different, and she had no idea who he was, so his image and wealth played nothing into this. Maybe he could still be seen as handsome even with a mask, but who he was wouldn’t be a factor.

“I’m alone,” he confirmed. “The question is what are you going to do with that information?”

Suddenly, her grin turned sharp and she walked closer, leaning in and whispering into his ear.

“I’m going to swallow down your cock and make you cum.”

Giovanni’s eyes widened, caught off guard by the sudden crudeness and of the abrupt sexual offer. Was it even an offer?

She grabbed his tie and started walking past him, making him follow after her.

  
Tossed into a bathroom, he incredulously watched her lock the door behind her before approaching him confidently, sinking to her knees and nonchalantly grasping for his belt.

“Wait,” he fumbled, needing to take a moment.

But she just gave him an impish smile and then unzipped his pants, reaching into his boxers and pulling out his cock. He could feel it throbbing in her grip, her slim hands curving around it before her painted lips moved forward and wrapped around the head. She moved down in a slow slide, letting his dick get wet from the cavern of her mouth, slick with spit and precum already dripping from his head and spreading because of her.

He watched in fascination, finding himself eye to eye with her, her pretty eyes open and watching him almost tauntingly.

Then she moved slowly all the way down his cock and let it slide down her throat, the _glug glug_ sounds coming from her throat making him harden in her mouth even more, while his jaw loosened as her red lips (red from lipstick and hard work cock-sucking) touched the base of his cock, kissing his skin and leaving a mark on him.

“Fuck,” he breathed out, utterly fascinated by the show.

She gave him a smug smirk around his cock and then began to move her head back, before swallowing him up once again. He licked his lips, turned the fuck on, and let his hips move to her rhythm.

She moved back, so did he. She moved forward, he moved his hips to meet her.

And then one of her hands reached for his balls, cradling them and caressing them roughly, making his hips stutter. She tugged on them, tickling them slightly, before she moved her mouth off his cock and moved her lips to his balls, licking large circles around each one and then mouthing them in a tight suck that caused him to grip her head and start letting out a string of Italian curses.

She stilled and he worried that he’d pissed her off or scared her off, something that would discontinue this. Instead, she moved her head up in his hands and stared him in the eye, then opened her mouth wide in offering.

He licked his lips. “You’re really something else, aren’t you?” he muttered, taking his cock and pushing the head of it passed her soft lips. He groaned and welcomed the feel of her hot, wet mouth again. “Shit, your mouth feels good!”

“Nggggh!” was all she could utter, mouth too stuffed to say anything.

Giovanni began moving his hips, keeping her head in place while he face fucked her, easily sliding down that throat of hers. He didn’t remember how long it’s been since he’d actually been turned on by a partner like this. But whoever she was, she was the first in a long while to really rile him up.

When he thrust into her mouth, she suddenly sucked nice and hard, making him jerk into her mouth, cumming without warning into it and shooting down her throat. She swallowed around his dick, and he watched intently as it happened, now utterly even more turned on than ever.

She let his cock out of her mouth with a soft pop, before grinning lazily at him.

“My turn.”

Blinking, he was surprised by her rising steadily and grabbing his legs to pull him down, pushing him back to lay on the ground and climbing onto him.

“What’re you —”

“Nm mm,” he saw her gather up the evening gown and bunch the hem at her waist, exposing black panties that she pulled down and off of her lean legs. “I said it was my turn.”

And then her knees were on either side of his head and her shaved, pretty little pussy was right above his face.

“Eat me up properly, won’t you?”

She sat down, smothering his mouth and nose with her cunt and experimentally shifting. Originally off guard, he then pushed his tongue into her opening and began slithering his way into her warm entrance.

Damn, she tasted sweet and her juices were spilling out rapidly, enough for him to try to drink mouthfuls of it. He moved his hands to her waist but let her control the pace, enjoying her squirming on top of him.

He traced her netherlips, eating up her pussy eagerly and letting her juices soak in his mouth, spilling over and coating his jaw and chin.

“Oh, oh!” she started moving faster, her voice going high. “Fuck! Arceus, I’m so freaking close. J-just a little bit more!”

He grabbed on tighter and held her still, letting his tongue thrust into her over and over, tongue fucking her until she came with a loud cry.

She jerked around in his hold, but he held her down, letting all of her juices and girl cum spill into his mouth.

When she relaxed and slumped in his hold, he let his hold lightened, only to be surprised by her rushing off of him, her gown falling easily to her ankles.

“Ah, time’s up,” she said in disappointment. “Cinderella’s got to go, you know?” she said playfully, her fingers slipping at the edges of her mask.

She threw it at his face, causing him to reach and catch it, busied by trying to keep it from hitting his eyes and blinded at that moment.

When he looked back to her, she was already gone.

Frowning, he carefully held the mask and then grinned as he found her panties still on the ground. He picked it up and grabbed it, hiding it in his pocket.

He was going to find out who she was.

Started 10/1/19 — Completed 10/1/19

**Notes for the Chapter:**

> I'm killing myself by doing Kinktober twice ;_:


	2. Day Two: Beg For It

**Notes for the Chapter:**

> 2\. Ass Worship | Begging | Medical play | Watersports  
Prompts Chosen: Begging, Medical Play
> 
> Playlist:  
Satellites by EMA

“Of course I’ll go to a party!”

Ash was beyond excited about this. If Looker needed a plus one to this masquerade ball, you could count her in!

She was almost eating her words later, when she was wandering around the ball though and mostly bored as heck. The music wasn’t really her type, the people she ran into were super snobbish, and Looker had ditched her a few minutes ago.

“Pfft! This is boring,” she grumbled.

Her eyes scanned the room, pausing only to find something —_someone_ —who caught her eye.

Dressed in a dark suit, tie and all, and obviously annoyed and wanting to be out of there, Ash knew that tall figure anyway. Slicked back hair, face obscured by a matching masquerade mask with red trimming, Ash knew without a doubt that that was Giovanni, Boss of Team Rocket.

She blinked and found a smile growing wide on her face. This…this was a good opportunity.

She had time and she found something to do and would keep her from being bored. Besides, he was a criminal so why else was he there but to be involved in criminal things?

Ash would only be doing her best to distract him, that’s all.

  
It’s been close to two weeks and Giovanni was waiting still. That girl, whoever she was, was stuck in his head and he couldn’t stop thinking about her. He was anxious to find out who she was.

And maybe continue where they left off.

A smirk threatening to spill out, he leaned back in his chair and closed his eyes. He let the image of her return to his mind, recalling that mischievous smile on red painted lips —the same lips that wrapped around his cock so confidently and also sweetly.

His cock swelled in his pants and he palmed himself a bit, before a ping! alerted him to a message from Dr. Zager. He sighed and focused on that instead, only to find himself grinning and eagerly looking at it. He opened the message and his grin faltered.

The results of the DNA match and search for his minx was in, but it wasn’t who he expected at all.

Ash Ketchum, bane of his Team and a constant obstacle, was the young woman he’d become rather obsessed with.

But she was an opponent and…sixteen.

He’d never messed around with a sixteen year old before and he didn’t plan to. He had plenty of women to sate his appetite. There was no need for him and that girl to mix up again.

Disappointed, Giovanni closed down the email and went back to work, reading mission reports while his cock had already deflated down with his mood.

  
Despite himself, he kept a closer eye on…Ash through the JJM reports. They’d been unusually serious and were doing good work, but he actually kind of missed their antics. Especially involving this girl…

_A flash of a mischievous smile in his mind._

He shook his head, dispersing his thoughts and walking through the hospital. At the corner of his eye, he spotted a certain girl and he stopped in his tracks. He hesitated, thinking about it. Then he sighed and made a decision.

Giovanni followed the direction she went to and caught up enough to see she’d entered a room. Narrowing his eyes in thought, he reaffirmed what he’d decided and approached the door, quickly opening it and slipping in, closing and locking the door behind him.

Her head moved up from where she’d been staring at the ground and her honey-hued eyes widened at seeing him. He forced a smirk on his face.

“Well, hello, Cinderella. It’s a long, long time from midnight this time, so we have plenty of time,” he practically purred as he approached her.

The wary look on her face became pinched as she realized what he was talking about. “Aa. So you know it was me that one night.”

“Imagine my surprise at being ambushed and sexually propositioned like that, and then to have the minx of a woman rush off the way you did,” he cornered her on the patient bed.

Since she’d sat on the edge of it, he made his way between her legs. She looked up blankly at him, revealing nothing.

“What are you going to do about it?” she asked casually.

It honestly frustrated him. _This_ was frustrating him! He didn’t know what he was going to do, what he was thinking. And the way she was so nonchalant, like she’d moved on and it was just another thing that had happened —It had driven him crazy and was still driving him crazy.

“What do _you_ want me to do? Punish you?” he sneered, angry at himself but masking it and directing it at her.

Then there was that mischievous smile on her face and she bent forward a bit, too close to him, just to stare in his eyes as she released and relocked the stirrups connected to the medical bed. She leaned all the way back, lying on it and planting her feet firmly into the stirrups, legs nice and wide.

“Depends,” she grinned, though he was dumbstruck at how she still (while being all seductive and sexy as hell) had a light blush on her cheeks. “If you’re going to punish me with your cock inside of me.”

He lightly shuddered and roughly pushed her against the medical bed. “You playing with me, girl?”

She only looked up at him, blinking with those long lashes of hers and those pretty eyes. “The only kind of play I’m interested in is a mutual, _consensual_, fun type of play.”

He hesitated one last time before he leaned in and immediately captured her mouth, locking lips and using his tongue to dominate her. She moaned into his mouth, letting her tongue lick at his lazily and submissively. His hand reached down, gliding down her clothed body until he reached her skirt.

“If you want me to play with you,” he taunted, “then I’m going to make sure you really want it. You’re gonna have to beg me for it.”

Her blush darkened, but before she could answer him, he slipped his hand under her skirt and found her panties, rubbing the pads of his fingers in rough circles around her clothed entrance. It wasn’t long until it became wet and he felt his fingers become lightly coated with her slick.

“Mm, you get wet easily,” he teased above her, watching her squirming and nibbling at her soft lips. He remembered those lips. “I like that. A lot.”

He wanted to know how wet he could get her, but he suspected he didn’t have enough time for that here.

“Hgggnn,” she closed her mouth and eyes tightly. That won’t do

He took his fingers away, making her whine. “I know you need to keep quiet, but keep your eyes open. I wanna see them hazed over in pleasure, _dolcezza_,” the endearment slipped out of his mouth, but he found he didn’t mind it and it made her face flush more.

She’d forced her eyes opened, staring into his eyes defiantly. That made him grin wildly and he returned his fingers right to where they were needed, rubbing her folds and slipping into her cunt. When she started to arch off of the examination bed and into his hand, he pulled his hand back.

“W-why’d you do that?” she asked in frustration, panting.

“I don’t hear any begging,” he smirked at her, taunting her even more as he brought his soaked hand to his mouth and licked his fingers, tasting her on them. He made a pleased sound. “Although you do taste delectable.”

Though that made her look embarrassed, she leaned back and kept her skirt flipped and out of the way, moving aside the thin material of her panties and having her fingers spread her pussy open to him.

“P-please continue, Giovanni. I-I want to cum.”

He chuckled darkly and spotted the stethoscope hung up with the other medical tools. Snatching it, he placed the ear parts into his ears and grabbed the sounding part (whatever it was) and placed it against her stomach, tracing it up her body and under her shirt.

“A-ah, that’s cold!” she exclaimed.

“Hmm, is it?” he said in distraction, listening to her body in interest. He ended up at her pounding heart and held it there. “Grab this and hold it right there,” he ordered her.

Though she hesitated, she did that and he moved and stood back, examining her wet, glistening, and slightly puffy pussy, rather pleased with himself.

“Hold it there,” he reiterated and then moved his fingers to carefully touch and examine her pussy. Her heart sped a little. “You’ve got such a pretty little pussy, don’t you,” he commented as he teasingly caressed and prodded at her cunt. “You even shave down here. Gives me such a nice view,” he licked his lips.

“S-shut up!” she said, clearly obviously embarrassed by now.

He lightly spanked her pussy, hearing her squeak while the sound of her heartbeat spiked. “Naughty.” He slipped in three of his fingers at once. “But you’re lucky I’m in a generous mood today.”

He started off slow but he eventually sped up, enjoying the sounds of his fingers thrusting into her with wet noises, her heartbeat speeding out of control, her barely controlled gasps and moans and pleas for him.

A final sharp thrust of four of his fingers into her sloppy cunt caused her to arch high up, body jerking practically off the bed. She’d lost her footing completely from the stirrups and he caught her as she sat up, cunt still twitching around his fingers and her hips gyrating for continued friction.

He grabbed his cock through his pants, fully hard and ready to enter her pussy, when there was a loud knock on the door.

“Miss Ketchum? The doctor will be here to see you shortly.”

“O-okay,” Ash shakily said, watching him uncertainly.

Disappointed again, though for a different reason, Giovanni sighed and helped her off the bed. She adjusted herself while he quickly ripped off the wrinkled paper cover from the medical bed and rolled down a new length for it.

He strode over to the door then, unlocking it and peeking outside. Seeing no one around, he glanced back at her.

“Until next time,” he smirked, hoping his voice and face wasn’t too much of a giveaway of how much he wanted to go on with her.

“Next time,” she said in return though, making him relax a little that the sentiment was reciprocated.

He left the room without looking back again.

Started 10/2/19 — 10/5/19

**Notes for the Chapter:**

> Gonna try to update all the current chapters I've written ;-;


	3. Day Three: Your Secrets and Lies are Mine

**Notes for the Chapter:**

> 3\. Sensory Deprivation | Temperature Play | Edgeplay | Knife Play  
Prompts Chosen: Sensory Deprivation
> 
> Playlist:  
Secrets and Lies by Ruelle

“You look distracted, sir,” his biggest confidant and friend commented, and he looked at Archer with a frown.

“Do I?”

Archer nodded, standing primly before him. “Yes. If I may be so blunt, Giovanni, you seem to be distracted a lot these days.”

It had been three weeks, one day, and six hours from the last time he’d last seen Ash Ketchum.

He was craving her every day since.

Giovanni saw his second hesitate. “Do you…do you want to talk about it?”

In his mind, he saw Ash spread out on his bed, bent over his desk, above him and riding his cock, and he didn’t want to share his fantasies with anyone. Part of him, even though he knew he wasn’t the best of men and was obviously a criminal, felt bad about those fantasies. He hadn’t forgotten how old she was.

_“P-please continue, Giovanni. I-I want to cum.”_

Reluctantly, he shuddered and felt mortified that he’d had the reaction in front of Archer. But remembering those words, how could he not want to be with her and give her what she wanted?

_“The only kind of play I’m interested in is a mutual, **consensual** fun type of play.”_

She had made it _clear_ that she wanted this, him, just as much. Why shouldn’t he take full advantage of all that?

“May I suggest accepting whatever it is that’s distracting? And going after it without any more hesitation?”

“Who says I was hesitating?” he snapped at the other, though he said nothing about accepting this strange obsession and attraction to a girl little more than half his age.

Archer stayed quiet, but his stare was unwavering.

Giovanni’s jaw clenched and he dismissed him. He rubbed his face with his hands roughly and stared up at the ceiling. But when his cell vibrated, he glanced at it before taking a double take.

An unknown number with the text of an address, the name of a hotel, and the room number.

A gut feeling told him who it was from and he was amazed that she’d got the nerve to send the text to him…and how she’d gotten his number in the first place. Part of him highly suspected the JJM unit…

But now the question for him was…did he go or ignore her?

  
He found himself heading straight to the city she was in, and looking for the hotel she was undoubtedly waiting for him at. It was a small modest one, nothing like the hotels he was used to staying in when he traveled. When he walked through, he looked around in paranoia, but no one looked his way or bothered him, so he headed towards the elevator and observe the floor numbers and the room number ranges were located near. Picking the 3rd floor, he waited until he was there and then walked around until he found the room. He stared at it contemplatively.

Then he knocked.

Without another second, the door opened and he slipped in silently. Blinking in the darkness of the room, he was caught off guard when he was pulled further in and then pushed against the closed door. Soft lips covered his and he moaned into her mouth, letting his hands move and search her hips out.

She pulled back from him though and he leaned in to recapture her lips, only to have something shoved into his mouth. Feeling the soft material with his tongue, with lace attached, he figured it was her panties. She pulled him from the door by his dress jacket and he was seated on the edge of the bed. He was still unable to see much of anything in the room, which made him uncertain.

“Hold still,” he heard her say quietly. “Don’t move. Don’t panic. I’m not going to do anything bad.”

And then Ash Ketchum put an actual fucking blindfold around his eyes and something that covered his ears. He was unnerved at the lack of noise and definitely being unable to see anything at all. Before, he’d been able to see slight movement, some shapes…but now he was struck blind and deaf and he didn’t know what she was going to do to him.

All of a sudden, he felt a wet tongue on his neck, licking slowly and moving from the side of it to the hollow of his throat. He shivered and gasped when her hands caressed down his chest and past his abs, slipping under his shirt and touching his skin. Her fingers touched lightly on it, trailing from his navel and scratching at the trail of hair there, before scraping her nails up his abs and to his pectorals, laying her hands flat on them while she moved him back and settled herself onto his lap.

He had no other clue what was going on, other than what she was currently doing to him. All of his main senses he’d relied on, sight and hearing, was gone and all he could focus on was the feel of her body, her fingers, her _breath_ until his mind was overloaded with _her_.

Ash rocked on top of him and he felt the bed sink and rise with every rock of her body, the warmth of her core through the cloth of his pants, the rise of his cock to meet her, and the wetness of her pussy leaking onto him. Then she pulled her panties out of his mouth and her lips were on his again and they were tangling tongues.

Everything felt so amplified and it made his heartbeat race in his chest. Blood was rushing through his veins and he was nearly high on adrenaline at this point.

“Shit, I wanna fuck you,” he said, even if he couldn’t hear himself say it.

If she replied, he couldn’t hear what she said back. Instead, he was pushed onto his back and he felt her unbutton his shirt, her tongue joining in and lathering kitten licks on his skin that he arched a bit into. He was greedy and he wanted more.

Her tongue found his nipples and he growled and reached for her when she started to lick at them and nibble lightly with her teeth. He wanted to return the favor, suckle on those tits of hers until he could see they were marked up and swollen because of him.

But then she pulled back completely to his confusion and frustration, especially as he had no idea what was going on. He was tempted to yank off the blindfold and whatever was covering his ears, when she pulled those off of him herself.

“I’ve disappeared a little too long,” he heard the disappointment in her voice. “I’m going to suck you off now.”

She squirmed down his lap to his ankles, where she unzipped his pants and began to pull out his cock. He felt her tongue lick and tease his head a little, wiggling at his slit and licking up the precum that quickly gathered at his tip. Her lips wrapped around his head and he heard her begin to suckle loudly.

“Fuck, yeah…Put a little more into your mouth,” he said and though she didn’t answer him verbally, more of his dick was swallowed up by her hot mouth, while one of her hands lazily wrapped around the rest of his cock and moved up and down it. Her other hand played with his balls and when she squeezed them, he bucked into her mouth.

“I’m gonna put my hand on the back of your head, okay?” he told her, reaching blindly for it and grasping the back of her head. He helped guide her into it, enjoying the blowjob and letting her go at her own pace. He knew she had to leave soon and he didn’t want her to, so he didn’t mind her slow pace if it meant her staying longer for it.

But she sped up and her hands was gone from his cock and balls, and going around still clothed legs. She buried her face right up against his crotch, letting her mouth swallow up his dick in one movement and tightening up her throat and sucking hard at his cock. He loudly groaned as he ejaculated down her throat, arching off the bed and pushing more of his cock down her throat and shooting ropes of cum down it over and over.

As she swallowed down his cum without complaint, he snatched off his blindfold and scrambled for his phone, turning on the flashlight and aiming it down at her —only to catch her finishing up, bobbing her head a little more to swallow down the last of his cum and then moving off of him, sitting up and licking her lips clean of leftover cum.

She blinked several times in the brightness of his flashlight, holding a hand up to give her eyes shade.

“Lamp’s to your left,” she offered and he reached over to turn it on, finally covering the room with some light. “I’ve got to go,” she said regretfully. “My friends called just now and are wondering where I’ve been.”

He nodded numbly, but when she moved to get off the bed, he reached for her and grabbed her hand.

“Do you want me to finish you off?” he asked quietly and she hesitated.

She glanced at her watch. “I’d like that, but…”

“Next time,” he promised.

Her lips quirked up. “Next time,” she said shyly.

And though he knew she’d just swallowed down his cum, he leaned up and kissed her slowly.

Started 10/6/19 — Completed 10/6/19


	4. Day Four: I'm the Bad Guy

**Notes for the Chapter:**

> 4\. Spanking | Mirror Sex | Spit-roasting | Dacryphilia (Crying)  
Prompts Chosen: Spanking, Spit-Roasting
> 
> Playlist:  
Haunted by Hope Murphy (Beyonce cover)

Ash was pretty peeved. After such a long journey to reach Nimbasa City, Team Rocket had to ruin things. All Ash wanted to do was let Cilan go off and be happy about the trains and relax, while she just hung back and enjoyed his enthusiasm.

But then there was this whole business with a ghost train and Meowth betraying them! And after she’d gotten to wrangle Giovanni’s phone number from the cat pokémon!

Kind of just pissed off about this now, she reached for her phone and went searching for the man’s number, calling him up.

She was itching to rile him up for this stupid situation Jesse, James, and Meowth had caused, and make Giovanni take responsibility for the trio’s actions for once.

  
Giovanni was working late for once. After Archer’s suggestion and that last time with Ash in that room, he’d taken to keeping an eye on where she traveled to and finding a place there to spend the time in while she stayed in the city. Just to keep close and to see if there was any time for them to cross paths…

It wasn’t like she was haunting his thoughts or anything.

His phone rang and he immediately reached for it. Pleased to see it was the girl he’d been thinking about, he was surprised and even more pleased to see that she had actually called him and not just texted. He answered and waited for her to speak first.

“So you answered,” she said with an amused tone.

“I did,” he leaned back into his chair.

“What’re you doing right now?” she asked curiously.

He glanced at his papers. “Working late. Nothing important though.”

“Hmm, is that so? What are you wearing right now then?”

He bit his lip. Was she just asking or…was she actually initiating phone sex?

“Just my usual dress suit,” he murmured, loosening his tie.

“I see…Wanna know what I’m wearing?”

“Yeah,” he said breathily. He licked his lips slowly. “Tell me. You wearing pajamas or you got something sexier on? Maybe you’re in your underwear?”

She laughed lightly. “I share a room with a 19 year old boy, so nothing too risque,” she said. He felt a bit jealous anyway, knowing that. Though while he wished he could imagine her in something sexy, he was glad she wasn’t wearing anything like that if she had to share a room with another male. “Just a large shirt that reaches my thighs,” she told him.

Still, he could imagine her long legs, the fact he could pull her shirt up and expose her, or even be able to have easy access to her like this…

“You know, you and your little Team caused some headaches and problems for me earlier,” she said casually. “Having to keep the pokémon from being stolen, having to chase that ghost train those idiot trio and that doctor scientist guy of yours had set up…I’m still a little hurt and peeved that Meowth lied and backstabbed us too. And after I managed to get your number from him! Here I thought the two of us were getting closer.”

He found himself feeling odd about that, though he knew she meant her and Meowth and not him and her. Still, he was feeling uneasy that she was grinning this up.

“At least I got to meet the Subway Masters,” she said nonchalantly. “They’re very cute. The reward for helping out with the situation was a great bonus too.”

“Reward?” he blurted out. He was starting to feel even more uneasy.

“Oh _yeah_. They’re twins, you know. I hate to use the stereotype, but who wouldn’t want to be sandwiched between two good looking people, especially twins?”

He scowled and tried to keep from imagining it.

“I mean Ingo and Emmet were spitroasting me for _hours_,” she said through the phone gleefully. “It felt so good to have their cocks in either end of me, pushing in and out of my mouth and pussy over and over.”

Giovanni’s hands clenched and he cursed his mind for conjuring the images. He could see her on her hands and knees, while the renowned Subway Masters plowed into her from either end, entering her mouth and her pussy at the same time. Her breasts were shaking from the movement, and she was moaning around one of the twin’s cocks.

“I didn’t realize how into double penetration I’d be,” she continued. “But it felt really good to be plugged up like that.”

“You enjoyed that, huh?” he growled into the phone, not willing to admit that just as he was jealous, he was also turned on by the image of her being fucked like that.

Not that he was okay with sharing her or any of this.

“Sure did,” she deadpanned and he scrunched up his eyebrows. “I lied, asshole. That’s what you get for ruining my day with your idiots.”

She hung up and he pulled the phone from his ear, to stare at it in disbelief.

Irritated, he got up from his chair and stormed out of his room.

  
When he found the Pokémon Center he knew she was staying in, Giovanni entered and searched out the entrance to the rooms. Thanks to his…surveillance, he knew what room she was staying in and where her traveling companions were. All he had to do was ask on his way there and the information was readily his.

He could do without the confirmation that she shared the room with the boy companion of hers.

Giovanni knocked firmly on her door and waited until she opened it. Her eyes widened at the sight of him, but he just muscled his way into the room and past her, before turning and yanking her away from the door. He glanced at her body and saw the shirt she’d been talking about, white cotton and indeed reaching her thighs.

Creamy thighs he wanted to grip and wanted to see wrapped around his waist.

“G-Giovanni?! What’re you doing here!” he heard her say.

Instead of replying, he sat on a bed and yanked her over, depositing her on his lap and quickly adjusting her to lay across it.

“Oof! Hey! What’re you —”

He raised his hand and then smacked her covered ass. She shrieked.

“You asshole! Are you _spanking_ me?”

“What a naughty brat,” he said in a bland tone. “Baiting and taunting me about a fake threesome and making me see things I didn’t. If _that_ was my punishment, _this_ is yours.”

Still, he didn’t raise his hand again and she stared up at him defiantly. “Well? What are you waiting for?”

“I don’t do things non-consensual. Ever. No matter what it is,” he said firmly, staring seriously at her and waiting for her answer.

He saw the hesitation on her face before she took a deep breath and relaxed on his lap. “Fine. Do it.”

Giovanni gave a smart slap against an ass cheek, causing her to yelp. She gave him an annoyed look that he smirked back at her for. As a soft apology, he lifted her skirt up and palm the cheek, waiting and admiring her ass. She had a nice, plump ass that he could fill his hands with. And he was right; he liked her wearing just a shirt like this —such easy access to her holes, which he took advantage of, letting a finger tease her folds.

“H-hey,” she squirmed on him. “I thought you were spanking me.”

“I am,” he said in distraction. He let his finger dip in a bit. While he slowly slipped it in, he used his other hand to deliver another slap, this time to her other ass cheek. “I’m going to get you off before your friends come back, since I couldn’t last time.”

She moaned as his finger thrust into her and he smacked her ass again. He could feel her cunt squeeze around his finger and smirked to himself.

He started lightly smacking her ass while he toyed with her pussy, feeling her juices soak out of her and her pussy repeatedly convulsing around his fingers over and over, especially as he started to add in more fingers.

“You were so bad earlier, weren’t you?” he told her, hitting her ass hard and feeling her pussy getting tighter.

“Y-yes,” she gasped out. “I was! I w-wanted to piss you off!”

“You did,” he said. “But you’re making it up so beautifully now, aren’t you?”

“Ha…ha…ha, y-es!”

He thrust in all four fingers and smacked her ass hard, and she came all over his hand while letting out a scream. He wondered if the room was soundproofed.

She slumped across his lap and he slowly let his fingers out of her sloppy cunt, pleased with himself.

“You have to go,” she muttered.

“I know,” he said.

Neither made a move to get up though.

After another minute or two, Ash got off of him and he reluctantly stood up. They exchanged another glance and then he was silently leaving the room again.

Part of him wondered what it’d be like to just not worry about having to get up from the bed and to just stay and relax on it, and eventually fall asleep together…

Started 10/6/19 — Completed 10/6/19


	5. Day Five: Can't Get You Out of My Head

**Notes for the Chapter:**

> 5\. Feet | Sadism/Masochism | Feederism | Shotgunning  
Prompt Chosen: Shotgunning
> 
> Playlist:  
Can't Get You Out of My Head by J2 ft. Sara Philips

Giovanni didn’t think that’d be the last of her he’d see in Nimbasa. It made him wonder what was next, what the two of them would get into together.

But then again, he never had any guarantees about anything.

“You have that look on your face,” Ariana commented and he glanced at her. “The one that says there’s something bothering you and you can’t keep your mind off of it.”

“Do I?”

Ariana gave him a look and he pulled a pack of cigarettes out that she raised an eyebrow at. “Oh, now I _know_ something’s up. You don’t normally smoke unless you’re really bothered or stressed, and even then it’s rare. What’s wrong?”

“Nothing’s wrong,” he said in agitation, even though that basically supported that.

Ariana huffed and rolled her eyes, obviously disbelieving that. He grunted and stood up irritably, snatching his jacket up and heading towards his door.

“I’m leaving,” he told her shortly. “I’ll go smoke outside in peace or maybe grab a drink at the hotel bar.”

She held up her hands, but he ignored her as he strode out of his suite and towards the elevator, continuing to ignore her as she silently joined him. The elevator stopped by the lobby floor and he was joined by his other Executives. By the look on his face, they kept silent and he said nothing to them as he lit up his cigarette and walked past them, heading to the hotel bar —only to stop short at seeing who else but the girl haunting him.

Ash Ketchum was looking around curiously in the lobby, sticking out in her casual jeans and shirt opposed to the richly dressed people around her.

He blinked and wondered if he was imagining this.

But then she turned and saw him and they locked eyes. Her lips, soft and pink, unpainted but still so enticing, smirked in glee.

“Shit, it’s that girl,” he heard Petrel mutter behind him.

His Team, by now, was well aware of her after the Idiot Brigade had continuously complained of her over and over around all the bases they’d been at. She was an annoyance that few even knew about, and even less knew what she looked like. His Executives knew of her only because they were to know about all possible threats, even as minor as her.

Part of him didn’t think she was a minor threat at all.

He could see her eyes travel to his Executives and then back to him, before heading over without any qualms. It made him tense and he was tempted to glance at his Executives.

To his surprise and confusion, she merely grabbed his arm and pulled him behind her as she headed back to his elevator, paying no attention to the Executives.

“H-hey!” Proton protested. “What the fuck are you doing with the Boss?”

“None of your business,” she answered without looking back.

Before anyone else could say something else or do anything, she and Giovanni were in the elevator and he saw her finally take a look at his subordinates, grinning wildly at them.

Then she looked back at him and took the forgotten cigarette, putting it to her own lips and taking a long drag, before leaning up while pulling his head down with her free hand, pressing her lips to his and letting the smoke blow into his mouth.

He inhaled sharply, both at the move and to instinctively breathe in the smoke.

The elevators closed then and he vaguely thought of his Executives, knowing they saw this and wondering about their faces.

Probably shocked as fuck and looking like idiots in the lobby.

Started 10/6/19 — Completed 10/9/19


	6. Day Six: Cast That Fucking Spell on Me

**Notes for the Chapter:**

> 6\. Daddy | Corset | Cock Worship | Biting  
Prompts Chosen: Cock Worship, Biting
> 
> Playlist:  
I Put a Spell on You by Annie Lennox (cover)

The doors closed and she wasted no time, taking the cigarette and squashing it to the floor of the elevator, continuing to kiss him through that smoke-filled kiss.

She pulled away, laughing lightly. “Bet your minions were left thinking ‘what the fuck’.”

“Probably,” he said. “But what in the world?”

Ash shrugged. “Wanted more of you and wanted to finally have time where there won’t be any interruptions. It’s my last night in Nimbasa before I head out with the others to Driftveil. I managed to figure out where you were staying and thought why the heck not?”

She started rapidly unbuttoning his shirt and he amusedly took off his dress jacket.

“You like red heads, don’t you?” she asked casually, starting on his belt.

He glanced at her in confusion, working on unbuttoning her shirt. “…Usually. I suppose you can say they’re my type,” he hesitantly admitted and wondered where she’d heard that from.

She hmmed, glancing up at him underneath long, dark lashes and hooded eyes. She then pushed him against a wall and leaned up against him, pushing her mouth against his neck and kissing and licking at it, sucking hard enough that he could feel it.

Her hot mouth was all over his neck, repeating those actions until he was sure that she’d marked his neck up everywhere and realized that was what she was trying to do.

Right at the juncture between his left shoulder and his neck, her teeth actually sunk in and he made a sound between a surprised yelp and moan, the unfamiliar pain actually making his cock jolt in reaction.

She didn’t relent then though, only continuing to make smaller bites around his neck, nips at his jaw and another light bite to his earlobe before she was whispering into it.

“I’m not a red head,” she told him.

“I know,” he said breathily. “And I don’t want you to be.”

“Good,” she said and then dropped to her knees to mouth at his cock through his pants, the bulge of it rising against the clothed material making it easier for her to take it in.

Her fingers worked at his button and zipper, belt already gone, and pulled out his cock. She let it hang free, glancing up at him with a wry grin.

“You know, I really did miss this cock while you were gone,” she teased. “I’ll make sure to make up for the absence.”

And then she leaned into it and began to lavish attention to it with her tongue, slow licks driving him crazy. She took her time to worship, licking every inch and holding it firmly as she made sure she didn’t miss a place on it.

She kissed the head of his cock and wrapped her lips around it gently, suckling at it like it was a lollipop she was savoring and taking her time with.

He groaned and leaned back against the elevator wall, thumping his head against it in agony.

“Fuck,” he cursed aloud. “Take your fucking time, won’t you.”

She laughed, his cock head vibrating with it, making him squirm and roll his neck, putting a fist to his forehead. Then she moved her lips off of his head and let them slide against the side of his dick, all the way to the base of his cock and nuzzling his groin. She did the same on the other side and then caught him off guard when she suddenly plunged her mouth over his cock.

She bobbed her head several times, sucking at the same time, and he was tempted to put his hands on her head. But he kept still, body strung tight as she worked him.

Ash sucked hard enough that he bucked into her mouth at the same time as he banged his head back, causing him to momentarily black out and see stars. He’d cummed into her mouth then and he finally grabbed her head, holding her still as his cum flooded her mouth and poured down her throat.

“Shit, that was good,” he panted, slumping against the wall.

She stood up just as the elevator door opened. She leaned against him, grinning.

“So…I see your room’s available.”

Giovanni returned her grin and leaned down, wrapping his arms around her legs and picking her up, carrying her into his suite.

Started 10/9/19 — Completed 10/9/19


	7. Day Seven: 'Cause You're Mine

**Notes for the Chapter:**

> 7\. Praise-kink | Body Swap | Aphrodisiacs | Incest  
Prompt Chosen: Praise-kink
> 
> Playlist:  
Earned It by The Weeknd

Giovanni took no time in kissing her senseless, not at all bothered by her having just swallowed down his cum. Fuck, that she did so (always did) turned him on and made him eagerly delve into her fucking gorgeous mouth and do his best to own it in every possible way.

Her legs, wrapped around his waist, tightened around him and her core rubbed against his stomach eagerly.

“You’re such a good girl, aren’t you?” he murmured against her neck, peppering it with kisses. “So, so good for me.”

She mewled, wiggling even more against him. Her hands grasped onto his shoulders and she started rocking against him.

“So good at sucking me off,” one of his hands traveled to her ass and grasped it, squeezing it and enjoying being able to grab a handful.

“Y-yes,” she gasped out. “I’ll suck you off whenever you w-want!”

Giovanni licked his lips. “Yeah? What a perfect mouth you’ve got, _dolcezza_. I want to make use of it all the time,” he purred, slipping his hand under her skirt and palming her ass more fully. “Then again, I want to make use of _all of you_.”

She moaned loudly, arching up against him. “You can do what you want with me! I-I’ll be a good girl for you!”

_Oh_, this is good. She seemed to have a praise kink, did she? Well, praise her he could keep doing, especially if she kept giving him such lovely reactions.

He carried her all the way to his room and laid her out on his bed, admiring her splayed out form before him.

“You definitely are such a good, pretty little girl, sweetheart,” he murmured, looking her over and watching her flush red from his gaze. “So, so pretty and eager to be my plaything, hm?”

He climbed over her, kissing her lips briefly several times. “You’re so good at pleasing me, darling. I think about you all the time,” he said, admitting to it while pretending it was all part of talk. “Let me reward such a good girl, huh?”

He moved down and spread her legs, looking over her exposed pussy with an eager, admiring gaze.

“Mmm, it’s so pretty,” he teased her. “I always enjoy the chance to just look at it and admire your pussy.”

Her cheeks turned dark red. “D-don’t say that,” she stuttered and he laughed, letting a finger gently trace it.

It twitched and he smirked.

“You earned this reward,” he said, smirk widening. “Enjoy it.”

Giovanni moved his face closer to her and widened his mouth, covering her entire cunt with it and letting his tongue sink into her velvet warmth.

Her juices, sweet and tangy, flowed easily and he moaned against her. She tasted and smelled so good, he could probably just eat her out for days.

“So good, Ash,” he kissed her pussy, licking at her clit. “I wanna eat you out all the time.”

“M-mmph!” Her bottom wiggled before him, her body and pussy squirming. “Please, Giovanni!”

He laughed, flattening his tongue and licking her pussy entirely. “Don’t worry. I’ll get you off.”

He took his time with her though, just as she did in the elevator, and enjoyed her squirms, her sighs, her moans, her light thrusts against his face, her juices flowing from her…

“More, Giovanni, more!”

He reached for her hips and held her down, speeding up a little and using his tongue to thrust into her core, alternating between tongue thrusts and licks that had her screaming and writhing in his hold.

Giovanni reached for her clitoris and began rubbing it quickly, and she ended up thrusting into his mouth, screaming as she orgasmed and he licked her clean.

“I suppose you can say that was just as much my reward too,” he chuckled darkly, licking his lips slowly and savoring her taste.

She glanced at him in embarrassment.

“Do you want to stay over?” he found himself asking and she looked surprised.

She hesitated before shaking her head. “I’ve got to go back. I’ve been…gone too long and I’ve still got to wake up with them to leave in the morning.”

Giovanni nodded, hiding the disappointment he was surprised he felt. She slipped off the bed and straightened herself up, before coming over to him.

She glanced up at him, fingering his neck.

“You know, you’re mine, got that,” she said suddenly, the words catching him off guard. “So no pretty red heads, even if they work under you.”

She brushed past him and headed towards the elevators, leaving him bemused and wondering about her words.

Started 10/9/19 — Completed 10/9/19


	8. Day Eight: If It's Gonna Be Violent Tonight

**Notes for the Chapter:**

> 8\. Blood/Gore | Prostitution/Sex Work | Fisting | Hate-fucking/Angry Sex  
Prompt Chosen: Hate-fucking/Angry Sex
> 
> Playlist:  
Without You by Ursine & Annaca

The plan had been a disaster.

To be honest, it had started out well enough. Giovanni was taken aback that he had managed to run into Ash during all this, but despite his lingering obsession with her and desire to be with her, he wasn’t going to let her stop him from continuing with his plans.

She’d had Meloetta with her and he had needed the pseudo-legendary.

He’d ignored her glares in the helicopter, though he was surprised at how hard it had been for him. He hadn’t realized how deep his obsession for her had run and it made him uneasy.

He hadn’t wanted to and hated that he’d had to threaten and force her into the force field box, holding her and Meloetta captive, but Ash had refused to stay away and give up the pokémon.

And though he’d successfully brought Tornadus, Thundurus, and Landorus under his control and he’d nearly come close to taking over Unova, he’d slipped up and looked into that damnable mirror, where it had taken over _him_.

Then he lost his mind and started to destroy the region, instead of taking it over.

He barely remembered what had happened after, only knowing through Jessie, James and Meowth that Ash and her friends had managed to fix things right and that Ash had personally taken him out and brought him from out of the mirror’s control.

Prior to this, he confessed to actually keeping a light correspondence with her, even though he hadn’t been able to meet up with her again since their last night together in Nimbasa.

But having sent her a quick text now and receiving nothing made him wince and worry.

Honestly, what was he expecting? He threatened to kill her (even if he hadn’t meant it) and tried to take over Unova and instead nearly destroyed it. Why would she contact him back?

Still, he sent her another text, telling her where he was staying and resting up at after that whole ordeal.

He hadn’t expected the knock that came at his door an hour later.

When he hesitantly opened it, there she was. But her face was blank and she didn’t look eager to see him or in a playful mood.

Instead, she stepped into the room and closed the door behind her solemnly.

Then she shocked him when she slapped him hard. But then she’d kissed him immediately after and he didn’t know whether to kiss her back to step away from her and demand answers.

He didn’t have to because she stepped back herself and shoved at him hard, glaring at him furiously.

“You’re so fucking stupid!” she screamed, hitting his chest hard, but she kissed his jaw straight after. To his bewilderment, tears sprung to her eyes. “You’re so fucking _stupid_!” she repeated.

Ash practically threw herself at him and he didn’t think she knew whether she wanted to beat him to pulp or kiss him senseless, alternating between battering his chest with her fists and swallowing his mouth into a needy kiss.

His hands found their way to her ass and he hauled her up, wrapping her legs around his waist. Her hands reached into his hair, grasping it harshly and violently tugging it. He could almost swear that she was close to ripping strands out of his scalp, it already burning from her assault.

When she bit down on his lip, she bit hard enough to draw blood and he reeled back from her.

“What the f —”

“_I hate you_,” she hissed at him, eyes glaring venom at him. “You should’ve died back then!”

That made him stop short and stare, not sure how to take that. He couldn’t even answer, even as she drove into him, mouth hot and heavy on his neck and hands nimbly unbuttoning his shirt.

He was lost in how to act when she was spitting vitriol and assaulting him, and then yet also turning him on with her plush lips, sweet mouth, and soft fingers that were oppositely harsh on his body.

She’d pushed him onto a chair and had quickly unbuckled his pants, wasting no time in taking his cock out and her hand rapidly grasping it and jerking him off to a hardened state. He inhaled sharply and before he could find time to take a breath, she’d clambered onto his lap and lowered herself onto his dick, impaling herself.

“You’re an asshole!” she yelled tearily and his hands automatically had reached for her waist. “A total bastard, you know that?!”

Her hand moved back and then slapped him, and she moved to do it again, though this time he had enough sense gathered to snatch her wrist up and stop her.

“Stop that!” he shouted at her, even as he thrust up into her.

“Fuck you!” she sneered, violently slamming down on him, which made him lose breath and throw his head back.

Her lips attacked his unintentionally bared neck, tender kisses he enjoyed before they were replaced by harsh bites.

“I should have let that mirror fuck you up,” she hissed into his skin. “You’re a shitty person, Giovanni!”

His hand still on her waist squeezed and he bucked up into her, letting go of her wrist to place his hand against her lower back to support her.

“I know,” he gasped out. “S-stop.”

“No,” she refused, gritting her teeth before reaching for his hair again and pulling it, making his head bend back and baring his neck again.

To his shock, she used her free to wrap around his throat and _squeeze_. His throat convulsed under her grip and he hesitated on whether to stop her or not. But the lightheaded sensation made his pleasure at her tight pussy grasping his cock heighten and he couldn’t help just letting her choke him while he went to grasp her hips and drive wildly into her warm cunt over and over until his cum spilled out of him and into her.

She let go of him then, but he still held onto her.

Started 10/9/19 — Completed 10/10/19


	9. Day Nine: Gimme Another Minute

**Notes for the Chapter:**

> 9\. Titfucking | Sthenolagnia (Strength/Muscles) | Bondage | Lingerie  
Prompt Chosen: Lingerie
> 
> Playlist:  
Without You (live) by Ursine Vulpine & Annaca

“Let go of me,” she said acidly, but he refused to do so, holding on even tighter. “I said —”

“This wasn’t how I wanted to have sex with you,” he said suddenly, making her still.

Ash looked at him with a scowl, but he actually looked back at her remorsefully. “I don’t have angry sex. I’m not even remotely interested in having hate sex of any kind and I definitely didn’t want that with you. It wasn’t supposed to be like this.”

She clenched her jaw, though she forced herself not to squirm with his huge cock still sheathed inside her.

“I don’t care,” she said, even though she knew it was a lie.

“I messed up,” he said and she wanted to scream at him that that was obvious.

“I don’t know what makes me angrier,” she felt herself give in a bit, slumping against him. “That you actually fucked around with legendaries, when I thought you were the only smart Team Boss not to do so, that you were an asshole to Meloetta and hurt her. Or that you…that you actually implied you’d kill me with that stupid box thing.”

She felt him take her head in his hands and kiss her forehead.

“I didn’t mean it. I swear.”

She couldn’t help wondering about that though.

  
The moment she slumped against him, he felt relief. It wasn’t like him, but he didn’t care right then. But as she lectured him (which he was glad for, rather than her spewing hate at him), he mentally winced, holding her closer to him.

Well, shit, he really did fuck up. This wasn’t an outcome he had predicted or wanted at all. Even though he admitted that he had wanted and had been close to taking over Unova, in the end it all just became a clusterfuck.

“You’re right,” he admitted. “I thought I had it all in order —and instead I almost lost too much.”

He was afraid to ask her if he’d…lost her. He didn’t want to admit to the emotion of fear of that, to admitting to his obsessive attachment to her. But deep down, in the darkest recesses of his mind, losing her wasn’t an option.

“I didn’t want to have sex with you like this,” he reiterated and it was the truth. They had not gone all the way before and to have their first be out of anger disappointed him.

He’d wanted much more out of it and to give her as good a time as she had unexpectedly brought him.

Picking her up suddenly and earning a yelp out of her, he carried her to his room and laid her down on the bed. She lay back, watching him warily, especially since he had yet to pull out from being inside her.

“I want to do this properly,” he murmured, looking her over.

He let his hands pull her shirt up, revealing her soft tummy. He had his fingers glide over it, making her squirm while he felt her soft skin.

Leaving her shirt there, her stomach bare to him, he moved to the hem of her skirt and pulled it up to her waist. She wore lacy red panties, with the underlining pulled to the side to where his cock had entered her.

Curious, he pushed her shirt up more and shifted his hips eagerly at the matching set of a lacy red bra that encased her perky breasts.

“Oh you do wear red well, _dolcezza_,” he licked his lips, eying her lingerie. “Though I am continuously surprised at your choice to wear lingerie. I never pegged you as the type.”

She lifted her chin defiantly. “I don’t do expectations.”

He laughed heartedly and bent over to kiss her fondly, letting himself start rolling his hips into her, moving his cock deliciously in and out of her cunt while he ripped her bra off of her and freed her tits.

“Mm, so hot and tight, sweetheart,” he murmured into her ear, gathering her up into his arms. “I want to make you feel as good as you make me.”

She sighed blissfully, arching into him. “Ah, ah! You do make me feel good!”

He flicked his tongue against her ear, bringing her up from the bed to hold her upright, thrusting up into her from this angle.

“I’m sorry,” he said softly against her. “I want you to feel so good. I’ll make up for earlier.”

She whimpered. “I’m sorry for hurting you earlier,” she gasped out. “I didn’t…I didn’t want to have sex with you like that either!”

A sense of relief flushed through him and he pulled her head to his, plundering her mouth with his tongue thoroughly, wanting to overwhelm her and make her lose her mind.

Her breasts pushed up against his chest and he grabbed one of them in hand, squeezing and enjoying the way it filled up his palm. He pulled at it, rubbing his thumb against a taut nipple and dipping his head to suckle on her other breast.

She made a high keening noise he was pleased to hear, and he continued to lavish attention on her breasts, wanting to mark it up like she’d marked up his neck the other time.

Giovanni still had those marks, even if some were faded.

They rocked against each other and his cock fit so well in her, like her pussy was made for him. He felt like they fit perfectly together and he didn’t want to shove his cock in anything but her cunt ever again.

Their tongues tangled together and he began speeding up, making her hands shoot to his shoulders and grasp tightly, trying to find purchase and keep support for herself, only failing and relying on him to hold onto her while she screamed in pleasure and let him ram into her.

“I’m going to cum inside you again,” he growled, the idea making him feverish. He already had before, but he didn’t want to focus on that time when it had been clearly angry sex and nothing at all what he’d wanted with her. Not like this, mutually pleasurable and full of wants and desires they should have never given into or acknowledged —should never have _had_.

She moaned at that, her pussy clenching tight and seemingly enjoying the idea. “Cum inside me!” she gasped out. “Cum inside all you want!”

That made him tense and thrust up into her, spilling his cum inside her tight pussy eagerly and continuing to thrust in and out and have her pussy milk his dick of all the cum he could pour into her.

When he finally stopped and paused to catch his breath, he held onto her while she grasped onto him, exhaustedly laying her forehead against his shoulder.

“What’re we doing?” she asked quietly.

“I don’t know,” he answered, because he really didn’t.

He was just sure he wanted her and wasn’t willing not to have her.

Started 10/10/19 — Completed 10/10/19

**Notes for the Chapter:**

> Pssst!
> 
> Yeah, I'm still working on this even though it's long past Kinktober XD
> 
> (To be honest, I had this chapter and the next already written and forgot all about them when I got wrapped up and lost into the Game of Thrones fandom...)


	10. Day Ten: I'm on Fire For You

**Notes for the Chapter:**

> 10\. Hair-pulling | Waxplay | Micro/Macro | Bonds (Telepathic or Empathic)  
Prompt Chosen: Waxplay
> 
> Playlist:  
Fuego by Eleni Foureira

He had gotten the text about her entering the Unova League Tournament. As she battled, he had watched her on the screen, texting congratulations when she won and then consoling her when she lost her final match. Top 8 was actually pretty impressive, considering she’d started out with new pokémon for the region (minus her Pikachu).

Something he’d actually noticed was a pattern with her.

Taking his phone, for once deciding against a text, he braved a phone call to her instead.

“You called.”

“I did.”

“…Need something?”

“Despite losing, you did well,” he complimented her. “Do you want me to be your consolation prize?”

She laughed. “You want to be?”

“Delightfully,” he smirked into his phone.

“Text me your hotel and your room,” she said and he hung up, doing so. By now, they both knew he was already in the same city as her.

Giovanni turned to his door and went over to unlock it, and then moved to an armchair in direct line of sight of it, settling down for a wait.

Approximately half an hour later, the door opened to admit her, and she leaned against the door frame in amusement.

“Just anybody could’ve walked in, you know,” she raised an eyebrow.

He leaned back in his chair and shrugged. “I was only expecting you.”

Her lips twitched and she entered the room fully, closing and locking the door behind her.

He stood up from his chair and strode towards her, meeting her halfway and leaning down to kiss her. She’d leaned up to kiss him as well, and their bodies melded together, familiar to each other and at ease.

Giovanni easily leaned down to pick her up, swinging her legs over his arms without leaving her lips. He’d carried her to his bed, intending to undress her and enjoy her body, when she stopped him.

“Wait a second,” she said, pushing away. “I want you to lie back.”

Giving her a questioning look, he did as she wanted and waited for her, giving her an amused look. But she merely just started unbuttoning his dress shirt and pushed it open, revealing his chest and abs to her.

“Hold still,” she told him, while grabbing something from her pocket. She pulled out a candle and a match and he watched her uncertainly. “It’s edible wax,” she saw him looking, revealing what she was holding. “Just…don’t move.”

She lit the candle before putting out the fire, then the two of them watched what she was doing closely. She nibbled her lip as she tilted the candle, letting the wax drip onto his pecs.

He hissed in surprise, the wax rather hot, but he didn’t move or say anything else, deciding to go along with her curious venture.

She hmmed in thought and leaned over him, her tongue darting out and licking at the wax on his skin. He shivered and she licked her lips, before she became a little more enthused and started licking off the wax off of him.

Giovanni groaned, shifting underneath her. “So good with that wicked tongue of yours,” he smirked at her, even as he started to lose breath.

Her cheeks turned red. “If anyone has a wicked tongue, it’s you,” she retorted, though neither of them could say whether she meant sexually or his usual silver tongue abilities. Maybe she’d meant both.

Ash brought the candle over to his stomach, letting the wax drip all over it and pooling near his navel. She ducked down and began lapping at the wax, licking all around his stomach enthusiastically. It made him admittedly squirm in the same way she was usually the one doing so.

Her tongue traced the trail of hair leading to the top of his pants, and he wished it was off so her tongue could continue its journey and find its way to his eager cock.

Getting an idea, he reached down and unbuckled himself.

“Ash, pour the wax over my cock,” he said and she looked hesitant.

“You sure? It’s hot,” she said awkwardly.

“If your tongue makes it all better, it’s fine,” he grinned and she rolled her eyes, though she smiled a little.

“Okay, okay. If you say so.”

He continued to unzip himself, pulling down his pants and his boxers, letting his cock bob free. He watched her take a deep breath, before she moved the candle over his cock and tilted it. The first time the wax hit his cock, he hissed and winced, and she looked at him warily. But after giving her a strained grin and a gesture to keep going, she poured wax on him again, and immediately soothed his dick with her blessed wet mouth.

It was a different, welcoming warmth to the hot liquid wax, and he hummed in pleasure. The contrast in that and in the contrast between pleasure and pain, mingling and differentiating, made his head swim.

Her tongue lathered heaven onto his cock while the wax slipped over his weeping cock in punishment. She poured more wax, before swallowing down his cock and humming around it.

“Arceus, flick my head more with that tongue, Ash,” he moaned, lifting his hips up.

Though she did that quickly (too quickly for his taste), she pulled away while he protested. Except she ignored him, relighting the candle before putting out the fire and pouring the rest of the wax all over his body, making him completely lose his breath. In that moment, she took advantage by moving over him and adjusting herself over his cock, holding it still and then moving her pussy onto it, slipping it in easily.

They shared moans and while she started lifting and dropping herself down on him, she leaned over and began to enthusiastically lick the wax off of him at the same time.

“Oh fuck,” he cursed. “You’re such an eager little thing, aren’t you?”

“Ngh, Giovanni! Your cock feels so good inside me,” she gasped out, her face twisting in pleasure. Her tongue flickered over his skin. “Mmmm~”

While she enjoyed the taste of him and the wax, he started to focus on driving into her, wanting to find release after the crazy, unorthodox pleasured torture she’d put him through.

“It’s your turn to hold still,” he muttered, holding her tight to him and starting to snap his hips faster and drive into her harder.

She clutched onto him and he continued to abuse her sloppy pussy, loving the sounds of his skin hitting hers, the wet slap of skin against akin and his cock slipping into her eager hole.

With a loud “Fuck!” he slammed in one last time and came into her, pulling her into a kiss.

“I enjoyed my consolation prize thoroughly,” she said dazedly.

He huffed slightly but laughed under his breath, kissing at her jaw fondly.

Started 10/10/19 — Completed 10/10/19


	11. Day Eleven: I Put My Money on Red

**Notes for the Chapter:**

> 11\. Object Insertion | Sounding | Cross-dressing | Tribadism/Scissoring  
Prompt Chosen: Cross-dressing
> 
> Playlist:  
Perfect Disaster by Drew

Giovanni had had to go back to Kanto for a bit, getting irritable with the amount of work he had to deal with and the stress that had gotten to him. He hadn’t realized how relaxed he’d become during the duration of his meetings with Ash.

Before he’d left, he’d left a message telling her where he was and was now trying to call her. He frowned as he realized she wasn’t answering his calls and hoped she hadn’t been pissed off about him disappearing on her.

“I left a message and let her know, didn’t I?” he muttered, trying again.

Finally he heard the sound that meant she’d answered and he rolled his eyes.

“About time. Geez, don’t tell me you’re upset that I —”

“Don’t talk to me.”

He scowled and felt himself get irritable. “What do you mean —”

Ash interrupted again, voice almost a whisper. “Detective Looker is in the room. Don’t say anything else. I’ll call you back later. After…after things have been settled.”

She hung up before he could say anything else and he looked at his phone dumbfounded. But then worry filled him and he wondered what the hell was going on. What did she get into?

Unbidden, the old reports of the JJM unit came back to his mind and he pursed his lips. He hadn’t…he hadn’t really taken those seriously; none of his Executives did and no one else who had bothered taking a peek did. They all assumed the trio exaggerated things, like usual.

But he wondered.

Giovanni found himself trying to get into contact with the JJM unit, knowing they were still in Unova after Operation Tempest, and had gone back to trailing Ash and her group. It took a bit, but somehow he’d managed to get them tracked down.

“S-sir?” James, his blue-haired subordinate, asked nervously.

“Those reports you used to give me…about all those times you trailed after that kid,” he said, not saying her name, given he wasn’t supposed to know or care so much about her. “How truthful were they? In regards to her, not your exaggerated roles,” he drawled.

Jessie chimed in, feeling more relaxed now that it seemed they weren’t in trouble and the call was about ‘the twerp’.

“Very truthful, sir! In fact, when it came to her, you can believe that anything crazy is due to her!”

Meowth joined the conversation. “She’s pretty good at being involved in everything, Boss. Most times, she actually ain’t meanin’ to, weird enough.”

Giovanni frowned to himself, feeling uneasy about their report, especially considering the glimpses of their past reports he remembered thumbing through.

Most especially now that something seemed to be happening with her now.

“Is there anything going on right now?” he asked, keeping his voice unaffected, though he was still short with them.

There was silence and he felt his nerves shoot up, feeling the silence foreboding.

“Team Plasma was totally wiped out,” Jessie said gleefully. “And we made sure of it! We took them down and they got busted by the International Police!”

“Yeah, Boss,” James eagerly continued. “We battled them down and made sure they were so beat down that the International Police had no problem rounding them up,” he boasted.

“You shoulda seen us, Boss,” Meowth bragged. “Those Plasma losers didn’t have a chance!”

Well, if International Police were involved and Ash had mentioned a ‘Detective Looker’ —Giovanni had recognized that particular IP Agent —as well as her usual track record…then he could definitely guess that something had happened between Ash and Team Plasma, and that she was in the middle of the ‘clean-up’ and was likely also being questioned of the events. And if he could guess what happened…looking back to her past run-ins with Teams, she had a habit of defeating them, so he could at least guess at that happening. Hopefully. It’s what usually happened in regards to her.

“Make a full report later,” he ordered them. “And have _full_ honesty!”

He hung up, knowing that those three would likely be a little more honest about their involvement in the whole thing, on paper rather than ‘in front of him’ to impress him. He took a deep breath then and shook his head. He was going to, unfortunately, wait for Ash to call him back.

In the meantime, he could make his way back to Unova and to wherever she was.

  
With his travel arrangements, he was actually able to be there in just under six hours, the usual travel time from Kanto to Unova on plane. Giovanni took his personal Abra teleport transportation platform over to Unova, and then found out where Ash was through the incoming JJM report about the recent events. From there, he took a helicopter from there to Ash’s current location. Then he found a hotel and waited anxiously (not that he’ll ever admit that). While he waited, he took advantage of the time to read the recent JJM report in full and then went back to reread some of their past reports.

Fucking Arceus, that girl got into _Trouble_. Like Trouble with a capital.

She was incapable of not getting involved, and every time there was something dangerous that put her life at risk. And that wasn’t even including all the Team encounters! Not _just_ his Team! For goodness’ sakes, she’s run into every Team of every Region definitively and has had a hand in bringing them down.

And, like JJM said, it wasn’t like she was meaning to. Somehow or other, she got drawn in, even without her say so.

“Fuck, this is a headache,” he pinched the bridge of his nose. 

The knock on his door distracted him and he narrowed his eyes. He wasn’t expecting company aside from Ash’s, and he hadn’t even told her he was back in Unova, much less where he was.

“Room Service!” was called out, distinctly male.

His eyebrows furrowed and he warily reached for the strapped gun to his side, gritting his teeth and moving slowly to the door.

“What was that?” he feigned having not heard the first time.

“Room Service, sir!”

He reached for the door and counted to three, before turning the handle and flinging it open, then reaching out to snatch the collar of whoever it was and yank them inside. Slamming the door close, he then shoved the intruder against the door and placed his gun by his side for ready use (though he didn’t immediately reveal it, in case it really _was_ ‘room service’).

“Well, isn’t this a nice greeting,” the boy said, the lid of the hat he was wearing obscuring his face.

Jaw clenched, he shoved him harder against the door. “I don’t take kind to intruders. Room service? Never ordered any and you don’t look like you work here.”

Faded jeans, worn sneakers. The plain black shirt hung loose on the boy’s slim frame and the hat he wore further hid the identity of his intruder.

He watched warily as the boy reached up to his hat and then lifted it off, flinging it off as long dark hair slipped away from the cap to slide down a familiar face, complete with cheeky grin.

“Hey.”

Giovanni gently let her down and moved back a step, still feeling off guard. She shrugged at him before she ended up straightening up her clothes, clearing her throat a few times before she began to speak normally.

“I had to sneak away from the hotel blockade they were keeping everyone at and Detective Looker was being pretty insistent on me especially staying. Ended up crossdressing and changing my voice, as you can see,” she grinned, spreading her arms out to display her unisex clothes. She grimaced. “I can’t be gone long, but Meowth let me know you were in the area and I found you.”

“Are you okay?” he asked instead of everything else running around in his head. She blinked. “You get into these things and I know the trouble you’re always in. I heard from the JJM unit that Team Plasma was taken down and I just read their report, but _are you okay_?”

Ash grimaced, running a hand through her hair. “I’m good. Now at least. I have a few scrapes and bruises, but don’t worry about it. I’ll live. And I’m sorry for being abrupt earlier, but with Detective Looker around, I hardly had any time to myself and was having trouble getting back to you without alerting him.”

“Why would he care if you called me?” Giovanni asked warily.

She winced. “Ah, your little stint here in Unova was noted heavily. No one knows you’re the Boss of Team Rocket or anything, but somehow it was pretty clear that I had a good view of the Rocket Boss’ face. I had to pretty much say I didn’t know who it was and didn’t have that much of a look, but Cynthia was there and one of the locals that was attached to Meloetta.”

Giovanni stiffened up. Cynthia Shirona was a renowned battler and Champion, with a good reputation. Even if they didn’t believe a no-name local about Giovanni’s status as the Rocket Boss, Cynthia’s word alone would be good enough to bring him down (or at least bring heavy, open and widespread suspicion on him).

“I asked them not to say anything,” Ash bit her lip. He looked at her, taken aback. “Back then, after it happened. I asked them not to say a word about who you were.”

But that was…

“You were angry with me then,” he dazedly pointed out.

“Didn’t mean I wanted you to get arrested,” she equally pointed out. “Look, I’ve somehow gotten to work with Detective Looker several times —I’m pretty sure he knows my patterns better than I do. And he _knows_ I have the unfortunate tradition of meeting every Team Boss in every Region, so there’s no _way_ I wouldn’t know Team Rocket’s Boss. And I’m pretty sure he’s wondering, after all the Bosses I’ve known and have been caught, _why_ I haven’t said who the Rocket Boss is. If he ends up working with Lance, I’m pretty damn sure fingers are going to be pointed your direction, which is why I’ve been trying _not_ to be in contact with you.”

“What do you mean about Lance?” he asked, clenching his jaw (but also wondering how she knew him).

Ash made a face. “Giovanni, you _do_ know it’s pretty much an open-secret that you are the Team Rocket Boss over in Kanto, right?”

He vaguely kind of knew that. It hadn’t mattered to him before because there was never any concrete proof and he’d always been careful, but he’d always known that most of the gym leaders and all of the Elite Four were thinking it.

“There’s never any proof of course,” Ash shrugged. “Lance has ranted to me about that enough,” again, how did they know each other and how close were they? “But Lance has always sworn he’d pin you down and has always suspected I’d known —the whole Mewtwo in Johto thing was kind of a big tip off and a near slip, but Misty, Brock and me had decided even then to just keep our mouths shut. He probably knows my patterns even better than Detective Looker too.”

“But why?” he was once again surprised by that revelation. “You didn’t know me then and I hardly even knew you existed.”

Ash swept passed him and heavily sat on the bed in the room, glancing around idly but obviously stalling.

“There were a bunch of reasons,” she finally started with, though she was looking away from him. “We didn’t think anyone would believe a bunch of kids like us over someone like you, not with your influence and resources. There was also that Team Rocket was actually pretty good with picking up strays and keeping them out of bigger trouble or ironically providing them with a place to stay and people to rely on. There’s honestly no telling where Jessie or James would be at, and you really don’t have to bail them out every time, especially for low ranked nobodies like them. They’re pretty stupid and plain idiots most times, but they’re honestly actually pretty good people,” her lips twitched.

Giovanni silently agreed and admitted he was a touch fond of them.

“We kind of figure you guys were low key enough and were better off being around than not, and that you were a better Boss than can be said of Bosses,” she admitted fondly, which actually made him smirk at her, even as he kind of felt a really unfamiliar warmth at her words.

And then the kicker.

An unexpected light blush colored her cheeks and she rubbed the back of her head.

“Geez, I had such a huge celebrity crush on you then, you know?” she admitted. “It kind of broke my heart to find out you were the Boss of Team Rocket, and even then I don’t think that stupid crush ever went away. I don’t know if it even _was_ a crush. Misty and Brock always insisted it was some strange, obsessive infatuation and when we were questioned about all the Team Rocket run-ins, we just…never said anything. Or more like, the first time I just floundered and they knew without anything being said, and they made some dumb excuse. After that, I stayed quiet and they followed me. You were just…you were just always that thing that was always up in the air and everyone knew about it but no one would say a word.”

Well shit, that just fucking both made his day and yet not know what the fuck to do with that.

So he walked over to her and pushed her onto the bed, straddling her lightly and towering over her slight form as he leaned over her. She looked back at him with wide eyes, but he just rolled his hips into her.

“Fuck, you know you make a pretty boy,” he just said instead, tracing her lips with his thumb before moving his hand down her clothed chest and to the hem of her shirt.

She surged up and grasped his collar, pushing up against him as their lips met passionately. Even with their clothes on, they slotted together perfectly and his hard cock lined up against her covered womanhood.

“T-take it off!” she gasped out, slipping her hand between their bodies and fumbling with her zipper.

He let her take care of her jeans while he unzipped his pants and let his cock out, and waited for her to wiggle out of her jeans. Seeing her wear simple cotton white underwear was still oddly arousing, and he took the lining of it and pulled it up, hearing her squeal as it yanked up against her slit. Licking his lips at her leaking cunt, he kept holding the lining upwards and used his other hand to feel her pussy up.

“_Merda_,” he inhaled deeply, eyes hooding while he admired her glistening pussy. “You’re so fucking wet.”

“_Leccami la figa_,” she gave him a sharp grin.

He barked out a laugh. “Oh? Someone’s been brushing up on their language skills…even if it is only to curse and say dirty things. You want me to lick up your pussy, baby? Alright.”

Giovanni duck his head closer to her cunt and let his tongue slide up her slit, pushing aside her lining to be out of the way as he worshipped her cunt.

“Fuck! Fuck yes!” she screamed, spreading her legs.

It was hot doing this with her half clothed and him mostly dressed. It also kind of reminded him back to the early days of their ‘relationship’, where they messed around and kept their clothes mostly on. It was a little bit nostalgic.

Letting his tongue wiggle into her, he used one of his hands to reach into her panties and search for her nub, finding her clit and pinching, earning another scream and a squirm of her hips. Sucking on her pussy, he pulled away and let his fingers work into her, immediately slipping three fingers and pleased to find her wet enough to accept them. Once he managed to thrust in four of his fingers, he took his cock and pumped it a few times before he placed the head against her entrance and nudged it in.

“Good?” he asked her and at her nod, he slid into her in one stroke, causing both of them to moan and their bodies to shudder.

She grabbed the back of his head, fingers threading through his hair and pulling. “Fast and hard,” she demanded and fuck if that didn’t get him harder inside of her and hot and bothered.

He pulled back just a bit before he slammed right into her, making her throw her head back and move her hands to hold onto his shoulders, letting him snap his hips into a punishing rhythm that they both enjoyed.

Her cunt was squeezing him tight and each thrust was causing her body to jolt and the bed to shake. He took his hands off of the bed and grabbed her thighs, spreading her wide and slamming his cock into her, feeling himself drive deeper into her slicked up pussy.

“Goddamn, Ash,” he groaned, closing his eyes and enjoying the feeling of being inside her. “I fucking missed this.”

Arceus, being gone for so long without her and even being in another Region altogether, that was horrible; more so now that he was reunited with her and feeling this again. 

“I’m going to cum,” she gasped and he growled, pulling out of her and ignoring her disappointed moans. Instead, he flipped her over and with her still surprised, lifted her ass up and pulled her panty liner up against her sensitive slit over and over.

“Fuck, fuck, fuck! What’re you doing?” she screamed and then without warning, he pushed back in, grasping her ass and squeezing.

He pulled her ass up higher and began pumping into her cunt faster, feeling his balls clench. She came first and then he was pouring into her, sighing as he curved his front over her back, nuzzling her ear.

“_Ti penso ogni giorno_,” he murmured, relaxed and content. All the stress and irritation from before was gone, and the worry for her assuaged from his mind.

“I don’t know what you said, but it sounds pretty,” she slurred tiredly, before she snuggled comfortably into the comforter. “I’mma sleep before I go sneak out…”

He grinned slightly and pulled out, watching in fascination, smugness and arousal as he watched his cum leak out of her pussy.

Giovanni took his fingers and slid the cum right back into her hole, letting his fingers slide in and move around lazily.

“Fucking mine.”

Started 10/11/19 — Completed 5/26/20

**Notes for the Chapter:**

> I swear to God I'm going to finish this before October XD Have to start a new Kinktober project then after all, right? LOLOL...
> 
> I think this is the longest chapter yet ¯\\_(ツ)_/¯


End file.
